Benzyl mercaptan → 2-(Benzylthio)-3-nitropyridine

HRID 513714

Reaction equation

HRID 513714 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH2:17]([SH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCO>[CH2:17]([S:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 5073002-(Benzylthio)-3-nitropyridineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 38 general procedure 92, 2-chloro-3-nitro-pyridine(2 g, 12.7 mmol), Na2CO3 (1.75 g, 16.6 mmol), benzylmercaptan (1.87 g, 15.1 mmol) and EtOH (20 ml) at 90° C. for 4 h gave the title compound (3 g, 96%) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Workup

  1. customat 90° C.
  2. customfor 4 h

Sources & evidence

ORD record
ord-29ad9f09c69c4c328a084f911264c85c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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